#------------------------------------------------------------------------------
#$Date: 2019-11-10 01:23:29 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/53/4515372.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4515372
loop_
_publ_author_name
'Song, Inho'
'Lee, Seung-Chul'
'Shang, Xiaobo'
'Ahn, Jaeyong'
'Jung, Hoon-Joo'
'Jeong, Chan-Uk'
'Kim, Sang-Wook'
'Yoon, Woojin'
'Yun, Hoseop'
'Kwon, O-Pil'
'Oh, Joon Hak'
_publ_section_title
;
 High-Performance Visible-Blind UV Phototransistors Based on n-Type
 Naphthalene Diimide Nanomaterials.
;
_journal_issue                   14
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              11826
_journal_page_last               11836
_journal_paper_doi               10.1021/acsami.8b01500
_journal_volume                  10
_journal_year                    2018
_chemical_formula_sum            'C28 H18 N2 O4'
_chemical_formula_weight         446.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-12-22 # Formatted by publCIF

;
_cell_angle_alpha                98.5520(12)
_cell_angle_beta                 102.7330(10)
_cell_angle_gamma                92.1280(11)
_cell_formula_units_Z            2
_cell_length_a                   8.3500(3)
_cell_length_b                   8.6060(4)
_cell_length_c                   15.3260(7)
_cell_measurement_reflns_used    6982
_cell_measurement_temperature    290(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.125
_cell_volume                     1059.51(8)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9261
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.127
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       Plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.76
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0651P)²+0.0633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             4147
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b01500_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4515372
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
N1 N 0.21099(14) 0.94564(17) 0.29030(9) 0.0573(3) Uani 1 1 d
N2 N 0.71129(14) 1.18484(14) 0.35161(8) 0.0504(3) Uani 1 1 d
O1 O 0.27065(16) 0.68939(15) 0.26383(9) 0.0806(4) Uani 1 1 d
O2 O 0.14593(15) 1.19884(16) 0.32007(9) 0.0815(4) Uani 1 1 d
O3 O 0.65686(16) 0.95684(14) 0.25127(8) 0.0791(4) Uani 1 1 d
O4 O 0.76724(15) 1.41317(13) 0.45153(8) 0.0688(3) Uani 1 1 d
C1 C 0.5090(2) 0.71762(19) 0.42955(11) 0.0570(4) Uani 1 1 d
C2 C 0.41848(17) 0.83995(17) 0.40182(10) 0.0498(4) Uani 1 1 d
C3 C 0.44220(16) 0.98882(16) 0.45779(9) 0.0446(3) Uani 1 1 d
C4 C 0.35144(16) 1.11596(17) 0.43165(10) 0.0477(4) Uani 1 1 d
C5 C 0.3761(2) 1.25978(19) 0.48718(11) 0.0564(4) Uani 1 1 d
C6 C 0.29717(19) 0.8164(2) 0.31385(11) 0.0582(4) Uani 1 1 d
C7 C 0.22865(18) 1.0930(2) 0.34420(11) 0.0576(4) Uani 1 1 d
C8 C 0.0891(2) 0.9218(3) 0.20150(12) 0.0705(5) Uani 1 1 d
C9 C 0.16432(18) 0.9585(2) 0.12539(11) 0.0620(4) Uani 1 1 d
C10 C 0.2159(3) 0.8399(3) 0.06915(15) 0.0848(6) Uani 1 1 d
C11 C 0.2799(3) 0.8738(5) -0.00221(17) 0.1033(8) Uani 1 1 d
C12 C 0.2939(3) 1.0260(5) -0.01775(16) 0.1022(9) Uani 1 1 d
C13 C 0.2473(3) 1.1440(4) 0.03861(17) 0.1057(8) Uani 1 1 d
C14 C 0.1807(3) 1.1099(3) 0.10927(14) 0.0870(6) Uani 1 1 d
C15 C 0.87895(19) 0.79273(17) 0.36477(10) 0.0504(4) Uani 1 1 d
C16 C 0.85448(16) 0.94924(16) 0.38705(9) 0.0444(3) Uani 1 1 d
C17 C 0.94233(15) 1.03753(14) 0.47003(9) 0.0402(3) Uani 1 1 d
C18 C 0.91814(16) 1.19792(15) 0.49487(9) 0.0438(3) Uani 1 1 d
C19 C 1.00620(19) 1.28117(18) 0.57608(10) 0.0510(4) Uani 1 1 d
C20 C 0.73387(18) 1.02657(17) 0.32368(10) 0.0511(4) Uani 1 1 d
C21 C 0.79586(18) 1.27607(17) 0.43315(10) 0.0498(4) Uani 1 1 d
C22 C 0.5885(2) 1.2626(2) 0.29038(13) 0.0605(4) Uani 1 1 d
C23 C 0.66117(18) 1.36790(16) 0.23644(10) 0.0513(4) Uani 1 1 d
C24 C 0.5585(2) 1.4640(2) 0.18832(12) 0.0686(5) Uani 1 1 d
C25 C 0.6173(3) 1.5579(2) 0.13511(13) 0.0840(6) Uani 1 1 d
C26 C 0.7789(3) 1.5582(2) 0.12978(13) 0.0816(6) Uani 1 1 d
C27 C 0.8833(3) 1.4665(2) 0.17844(13) 0.0710(5) Uani 1 1 d
C28 C 0.8248(2) 1.37124(19) 0.23151(11) 0.0574(4) Uani 1 1 d
H1 H 0.491(2) 0.616(2) 0.3884(12) 0.067(5) Uiso 1 1 d
H5 H 0.314(2) 1.345(2) 0.4691(11) 0.070(5) Uiso 1 1 d
H8A H 0.009(3) 1.001(3) 0.2130(14) 0.096(6) Uiso 1 1 d
H8B H 0.047(3) 0.807(3) 0.1893(14) 0.092(6) Uiso 1 1 d
H10 H 0.203(3) 0.738(3) 0.0837(16) 0.105(8) Uiso 1 1 d
H11 H 0.317(3) 0.792(3) -0.041(2) 0.142(11) Uiso 1 1 d
H12 H 0.338(3) 1.051(3) -0.0675(17) 0.120(8) Uiso 1 1 d
H13 H 0.252(4) 1.259(4) 0.030(2) 0.161(12) Uiso 1 1 d
H14 H 0.145(3) 1.193(3) 0.1459(16) 0.112(8) Uiso 1 1 d
H15 H 0.819(2) 0.7325(19) 0.3076(12) 0.064(4) Uiso 1 1 d
H19 H 0.985(2) 1.393(2) 0.5902(11) 0.066(5) Uiso 1 1 d
H22A H 0.525(2) 1.321(2) 0.3277(12) 0.071(5) Uiso 1 1 d
H22B H 0.514(3) 1.172(2) 0.2441(14) 0.095(6) Uiso 1 1 d
H24 H 0.445(3) 1.465(2) 0.1940(13) 0.084(6) Uiso 1 1 d
H25 H 0.546(3) 1.624(3) 0.1037(16) 0.108(7) Uiso 1 1 d
H26 H 0.817(3) 1.627(3) 0.0928(15) 0.110(7) Uiso 1 1 d
H27 H 1.002(3) 1.466(2) 0.1749(14) 0.099(7) Uiso 1 1 d
H28 H 0.902(2) 1.3062(19) 0.2656(11) 0.067(5) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 C6 124.82(14) . .
C7 N1 C8 118.03(15) . .
C6 N1 C8 117.14(16) . .
C21 N2 C20 125.06(12) . .
C21 N2 C22 117.16(13) . .
C20 N2 C22 117.77(13) . .
C2 C1 C5 120.42(15) . 2_676
C2 C1 H1 117.8(10) . .
C5 C1 H1 121.8(10) 2_676 .
C1 C2 C3 119.81(14) . .
C1 C2 C6 120.53(14) . .
C3 C2 C6 119.66(13) . .
C4 C3 C2 121.24(14) . .
C4 C3 C3 119.08(17) . 2_676
C2 C3 C3 119.68(16) . 2_676
C5 C4 C3 120.33(15) . .
C5 C4 C7 120.21(14) . .
C3 C4 C7 119.46(14) . .
C4 C5 C1 120.68(14) . 2_676
C4 C5 H5 119.8(10) . .
C1 C5 H5 119.6(10) 2_676 .
O1 C6 N1 120.74(16) . .
O1 C6 C2 122.03(15) . .
N1 C6 C2 117.22(14) . .
O2 C7 N1 121.02(15) . .
O2 C7 C4 121.41(16) . .
N1 C7 C4 117.57(13) . .
N1 C8 C9 112.38(13) . .
N1 C8 H8A 101.9(12) . .
C9 C8 H8A 109.7(12) . .
N1 C8 H8B 106.3(12) . .
C9 C8 H8B 109.8(12) . .
H8A C8 H8B 116.6(18) . .
C14 C9 C10 118.2(2) . .
C14 C9 C8 120.91(19) . .
C10 C9 C8 120.8(2) . .
C9 C10 C11 120.5(3) . .
C9 C10 H10 114.7(14) . .
C11 C10 H10 124.8(14) . .
C12 C11 C10 120.4(3) . .
C12 C11 H11 119.0(18) . .
C10 C11 H11 120.6(18) . .
C13 C12 C11 119.6(2) . .
C13 C12 H12 119.4(15) . .
C11 C12 H12 121.1(15) . .
C12 C13 C14 120.1(3) . .
C12 C13 H13 123.2(18) . .
C14 C13 H13 116.6(18) . .
C9 C14 C13 121.2(2) . .
C9 C14 H14 120.3(15) . .
C13 C14 H14 118.5(15) . .
C16 C15 C19 120.35(14) . 2_776
C16 C15 H15 120.4(10) . .
C19 C15 H15 119.2(10) 2_776 .
C15 C16 C17 120.55(13) . .
C15 C16 C20 119.91(13) . .
C17 C16 C20 119.54(13) . .
C18 C17 C16 121.62(13) . .
C18 C17 C17 119.34(15) . 2_776
C16 C17 C17 119.04(15) . 2_776
C19 C18 C17 120.30(13) . .
C19 C18 C21 120.18(12) . .
C17 C18 C21 119.52(13) . .
C18 C19 C15 120.42(14) . 2_776
C18 C19 H19 117.2(10) . .
C15 C19 H19 122.3(10) 2_776 .
O3 C20 N2 120.76(14) . .
O3 C20 C16 122.20(14) . .
N2 C20 C16 117.04(12) . .
O4 C21 N2 120.19(14) . .
O4 C21 C18 122.60(14) . .
N2 C21 C18 117.21(12) . .
N2 C22 C23 114.53(13) . .
N2 C22 H22A 106.8(11) . .
C23 C22 H22A 110.8(10) . .
N2 C22 H22B 106.3(11) . .
C23 C22 H22B 107.8(11) . .
H22A C22 H22B 110.6(15) . .
C28 C23 C24 118.43(15) . .
C28 C23 C22 123.19(13) . .
C24 C23 C22 118.36(15) . .
C25 C24 C23 120.66(19) . .
C25 C24 H24 121.1(12) . .
C23 C24 H24 118.3(12) . .
C26 C25 C24 120.26(18) . .
C26 C25 H25 120.4(14) . .
C24 C25 H25 119.3(14) . .
C25 C26 C27 119.93(18) . .
C25 C26 H26 118.5(14) . .
C27 C26 H26 121.5(14) . .
C26 C27 C28 120.1(2) . .
C26 C27 H27 120.5(12) . .
C28 C27 H27 119.4(12) . .
C27 C28 C23 120.62(16) . .
C27 C28 H28 118.5(9) . .
C23 C28 H28 120.9(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.391(2) .
N1 C6 1.396(2) .
N1 C8 1.490(2) .
N2 C21 1.3982(19) .
N2 C20 1.3983(19) .
N2 C22 1.4809(19) .
O1 C6 1.220(2) .
O2 C7 1.2154(19) .
O3 C20 1.2099(18) .
O4 C21 1.2167(17) .
C1 C2 1.383(2) .
C1 C5 1.399(2) 2_676
C1 H1 0.985(17) .
C2 C3 1.413(2) .
C2 C6 1.479(2) .
C3 C4 1.411(2) .
C3 C3 1.416(3) 2_676
C4 C5 1.374(2) .
C4 C7 1.479(2) .
C5 C1 1.399(2) 2_676
C5 H5 0.953(18) .
C8 C9 1.507(2) .
C8 H8A 1.00(2) .
C8 H8B 1.02(2) .
C9 C14 1.369(3) .
C9 C10 1.380(3) .
C10 C11 1.381(3) .
C10 H10 0.95(2) .
C11 C12 1.371(4) .
C11 H11 0.95(3) .
C12 C13 1.358(4) .
C12 H12 0.96(3) .
C13 C14 1.384(3) .
C13 H13 1.02(3) .
C14 H14 0.94(2) .
C15 C16 1.374(2) .
C15 C19 1.407(2) 2_776
C15 H15 0.969(17) .
C16 C17 1.4116(19) .
C16 C20 1.487(2) .
C17 C18 1.4104(19) .
C17 C17 1.422(3) 2_776
C18 C19 1.377(2) .
C18 C21 1.485(2) .
C19 C15 1.407(2) 2_776
C19 H19 0.986(17) .
C22 C23 1.508(2) .
C22 H22A 0.967(19) .
C22 H22B 1.05(2) .
C23 C28 1.384(2) .
C23 C24 1.385(2) .
C24 C25 1.379(3) .
C24 H24 0.97(2) .
C25 C26 1.370(3) .
C25 H25 0.94(2) .
C26 C27 1.371(3) .
C26 H26 0.97(2) .
C27 C28 1.384(2) .
C27 H27 1.01(2) .
C28 H28 0.984(18) .
